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Holiday Homes in Stephentown

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Stephentown holiday homes

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

1. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.8 out of 10, Exceptional, (7 reviews)
"The host was extremely communicative and went above and beyond to ensure guest comfort."
United States
Diego G.
The price is NZ$990
includes taxes & fees
3 Nov - 4 Nov
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

2. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"Awesome location went for a solo trip w the purpose of spending time alone in nature with myself and god got exactly that calm quiet beautiful scenic area great room and service would book again"
United States
Varun M.
The price is NZ$367
includes taxes & fees
4 Oct - 5 Oct
NEW RENO - Chalet-style farm loft near Tanglewood
A spacious living room with a dining area, a kitchen, and a large window.

3. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is NZ$403
includes taxes & fees
5 Oct - 6 Oct
1800s Carriage house in Berkshires / Hudson Valley
Pool

4. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very good, (10 reviews)
"The owner was responsive. The heater worked well. The living spaces are as advertised. Traveling with 5 adults and a toddler; the layout is great. Convenient location for day trips and hiking."
United States
Maura L.
The price is NZ$962
includes taxes & fees
4 Oct - 5 Oct
Comfortable Berkshires retreat on mtn resort, SISO
A white two-story house with a porch, surrounded by trees and a hill.

5. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
United States
Christine C.
The price is NZ$880
includes taxes & fees
7 Oct - 8 Oct
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

6. Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (22 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is NZ$1,986
includes taxes & fees
3 Nov - 4 Nov
Hancock Village Inn Near Jiminy Peak
A wooden deck with a table and chairs, surrounded by a white railing.

7. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
8.4 out of 10, Very good, (10 reviews)
"Very comfortable and clean accommodations in a nice neighborhood, and a great deck to appreciate the view."
United States
Stephen L.
The price is NZ$883
includes taxes & fees
13 Oct - 14 Oct
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
A wooden kitchen with a central island, bar stools, and a dining table with chairs.

8. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (9 reviews)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
The price is NZ$387
includes taxes & fees
19 Oct - 20 Oct
Cozy Home in Pownal VT
A modern, semi-circular wooden cabin with large windows, surrounded by lush greenery.

9. Treat yourself at the stunning June Farms Wellness Huts!

Treat yourself at the stunning June Farms Wellness Huts!
West Sand Lake
10.0 out of 10, Exceptional, (8 reviews)
"Loved the wellness hut. Our sauna didnt work however the room was spacious and comfy. The staff is very attentive and we also enjoyed the soup stroll. Would def recommend."
United States
Lauren C.
The price is NZ$974
includes taxes & fees
12 Oct - 13 Oct
Treat yourself at the stunning June Farms Wellness Huts!
A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

10. NEW RENO Historic Creamery in Berkshires w/hot tub

NEW RENO Historic Creamery in Berkshires w/hot tub
New Lebanon
10.0 out of 10, Exceptional, (8 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveller
The price is NZ$1,007
includes taxes & fees
27 Oct - 28 Oct
NEW RENO Historic Creamery in Berkshires w/hot tub
A modern living room with a grey sectional sofa, a brown leather ottoman, a woven rug, a dining table with chairs, and a view through large windows.

11. Ellie’s Overlook, best view in the Berkshires!

Ellie’s Overlook, best view in the Berkshires!
Richmond
The price is NZ$1,198
includes taxes & fees
3 Nov - 4 Nov
Ellie’s Overlook, best view in the Berkshires!
A modern building with a wooden deck and a door.

12. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (5 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
The price is NZ$1,083
includes taxes & fees
5 Oct - 6 Oct
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
A kitchen with a wooden countertop, white cabinets, and red chairs. There is a staircase leading to another room.

13. Riverfront Rustic 1824 Mansion

Riverfront Rustic 1824 Mansion
Troy
9.0 out of 10, Wonderful, (14 reviews)
"Loved the house! So much character and in a great location! "
United States
Alex V.
The price is NZ$406
includes taxes & fees
5 Oct - 6 Oct
Riverfront Rustic 1824 Mansion
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

14. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Williamstown
10.0 out of 10, Exceptional, (2 reviews)
"Easy breezy, short walk to walk into town/Williams Campus. Down to Earth, yet sophisticated vibe, great art scene. "
United States
Michelle B.
The price is NZ$1,056
includes taxes & fees
3 Nov - 4 Nov
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A modern, semi-circular wooden cabin with large windows, surrounded by lush greenery and trees.

15. Treat yourself at the stunning June Farms Wellness Huts!

Treat yourself at the stunning June Farms Wellness Huts!
West Sand Lake
10.0 out of 10, Exceptional, (8 reviews)
"The wellness hut was an amazing getaway. Beautiful interior and design. Loved the little outdoor sauna. Loved the front porch/deck. Would definitely return for another stay."
United States
SteveS
The price is NZ$851
includes taxes & fees
3 Nov - 4 Nov
Treat yourself at the stunning June Farms Wellness Huts!
A spacious room with a wooden ceiling, large windows, and a chandelier.

16. Luxury Barn Retreat — All-Season Escape Awaits!

Luxury Barn Retreat — All-Season Escape Awaits!
East Chatham
10.0 out of 10, Exceptional, (3 reviews)
"Peaceful weekend spot"
United States
Michael T.
The price is NZ$1,309
includes taxes & fees
7 Oct - 8 Oct
Luxury Barn Retreat — All-Season Escape Awaits!
A camping setup with a metal chair and a table by a river in a forest.

17. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (15 reviews)
"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"
United States
Jess S.
The price is NZ$608
includes taxes & fees
3 Nov - 4 Nov
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A wooden cabin with a curved roof, two windows, and a door, surrounded by a garden and forest.

18. June Farms is like no place else on earth! "My New Happy Place" is a comment we hear quite often

June Farms is like no place else on earth! "My New Happy Place" is a comment we hear quite often
West Sand Lake
9.8 out of 10, Exceptional, (9 reviews)
"We loved our stay here - it was beautiful, well appointed, and relaxing!"
United States
LauraS
The price is NZ$932
includes taxes & fees
2 Nov - 3 Nov
June Farms is like no place else on earth! "My New Happy Place" is a comment we hear quite often
A modern kitchen with white cabinets, a wooden countertop, and a large TV mounted on the wall.

19. Spacious 4 Bedroom Home • Sleeps 8 • Private Yard • Near Hopitals • FREE Parking

Spacious 4 Bedroom Home • Sleeps 8 • Private Yard • Near Hopitals • FREE Parking
Pine Hills
9.8 out of 10, Exceptional, (8 reviews)
"The house was nicely setup and clean. The location was very central to where we needed to be. The host was very responsive. "
United States
Elizabeth P.
The price is NZ$733
includes taxes & fees
21 Oct - 22 Oct
Spacious 4 Bedroom Home • Sleeps 8 • Private Yard • Near Hopitals • FREE Parking
A kitchen with white cabinets, a wooden dining table, and pendant lights.

20. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (61 reviews)
"Cute and comfy home. We enjoyed the unique decor and lack of TVs everywhere. It was a great break from all the crazy. Lots of conversation and togetherness."
United States
Diane
The price is NZ$861
includes taxes & fees
13 Oct - 14 Oct
A roomy remodeled retreat close to MassMoCA
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Stephentown Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

8/10 Good
"I have stayed here multiple times. My unit this trip was very clean, well equipped and comfortable. The check in process and front desk staff were terrific. My only issue was a strong smell of marijuana coming through the slider and bedroom window . The staff gave me a fan to blow the smell back out however it was an issue throughout my stay."
Susan 7-night trip
Posted 1 hour ago
Berkshire Mountain Lodge

Find out more about Stephentown

Stephentown Holiday Homes information

Number of reviews
194
Accommodation
303 Holiday Homes
Lowest Price
NZ$367
Highest Price
NZ$1,986